Permanent Records is an ongoing closer look at the records that matter most.

Gang Starr released six records between 1989 and 2003, and four of them are stone-cold classics. Quibbling about which one is the actual best is an all-time-great way to piss off a bunch of rap nerds. DJ Premier is on the short list for greatest producers in the history of the form, a microscopic technician whose deep crates and minimalist drums remain a definition of hip-hop purity, and Guru was his muse, the monotone master who rapped in sharp quotables. But there were other great MC-DJ combos out there; part of what makes Gang Starr’s great run so indelible is the albums themselves, which are designed with a front-to-back cohesion that stuck out during the glut of great hip-hop in the late ’80s and early ’90s. To release one 20-track album without a dud is a feat—but to release four in a row?

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Part of this has to be attributed to the holistic manner in which the duo conceived the records. In an interview commemorating the 20th anniversary of ’94’s Hard To Earn—see, they’re all worth commemorating—DJ Premier explained their creative process. Before he even started making beats, he said, “Guru would always give me a list of titles. He would have the whole album mapped out.” He’d have tiny notes saying the rough topic of the track—“‘Tonz ‘O’ Gunz,’ this is about all the guns in the streets”—or even describing which ones should be singles. We generally think of musicians just “creating music,” then coming up with packaging and titles later. In hip-hop, producers often bank dozens or even hundreds of beats for a rapper to comb through in search of a record. Gang Starr did this backwards, starting with titles, then beats, then verses. When we look at the Gang Starr discography, which some of us still do pretty much weekly, what we’re looking at is something uniquely designed, each track list telling a self-contained story and each album title conveying a message specific to its moment. Step In The Arena was the moment Premier and Guru proved themselves; career-ender The Ownerz was designed as a capstone.

I was thinking about this recently while relistening to Moment Of Truth, which turns 20 at the end of this month, and which is, infinite rap-nerd arguments be damned, their actual best album. Okay, okay: It’s my favorite, how about that. In ’98, it arrived at a weird time for hip-hop at large, when the roar of the East-West feud was fading and along with it the last vestiges of the mythic golden age. Producers were rifling through vintage funk and soul records for samples less and less in favor of the synthesized bombast of Swizz Beatz. In the South, the No Limit empire was ascendant, so much so that Snoop dropped an album with a Pen & Pixel cover. Method Man inaugurated the second wave of Wu-Tang solo releases by trying to rap like he was from the future. There were great albums being released—JAY-Z stepped out as a star on the smash Vol. 2… Hard Knock Life, and Outkast achieved immortality on Aquemini—but these albums point to the strange period of flux hip-hop found itself in. Artists were either reaching back toward the past, or striving toward some hazy, post-millennial future.

Moment Of Truth seemed uniquely aware of this. It was something of a comeback record for Gang Starr, arriving four years after their previous release, and at a time when their particular brand of hip-hop was becoming anachronistic. But for the duo itself, it represented a quantum leap forward. The jazz rap pioneered on early records gradually morphed into something denser by Hard To Earn, incorporating any sonic touchpoint that lit up Premier’s ears, but by Moment Of Truth he was weaving together disparate elements into sonic tapestries of unsurpassed complexity. Sometimes this was toward purely rhythmic, almost mechanical ends; “Work” combines triumphant horn blasts, far-off sirens, plunking upright pianos, and drums that sound like they were recorded in an abandoned factory into a weird-ass Rube Goldberg machine of a beat. But more often he was blending things toward a much richer emotional end, creating a woozy blanket of brass on “Next Time” that almost makes Guru’s battle raps and a scratched, spectral LL Cool J vocal clip seem mournful, even doomed.

Throughout, Primo creates hooks like this, scratching together dense montages of lines from other rappers into custom-made choruses. (“You Know My Steez” alone cuts together Method Man, Public Enemy, Das EFX, and Grandmaster Flash.) He didn’t invent this technique, nor was Moment Of Truth the first time he employed it, but it adds to a sense of fullness to the record, a sort of imperative to its mission that’s complemented by the fullest guest list in the group’s discography. Inspectah Deck shows up to bomb atomically on “Above The Clouds”; Scarface thunders in like an Old Testament god on “Betrayal”; Krumb Snatcha’s verse on the swooning “Make ’Em Pay” got a hip-hop quotable from The Source, back when that was a head-turning plaudit.

But for all Primo’s sonic invention, it’s Guru who steps out on Moment Of Truth, using this backdrop to release the most complex, fully authored lyrical performance of his career. He was 31 when the record came out, which is also, scientifically speaking, the exact moment that you are unequivocally old, but rather than keep trying to move from “Ex Girl To The Next Girl” he wrote a full album from that strange vantage point of non-youth. It’s a more remarkable text than it gets credit for, an 80-minute classicist hip-hop record about growing older, detailing the rare points in life when time stops swirling and you can see the past and future with something akin to clarity. There are times when that sounds like grown-man wisdom, as on “My Advice 2 You”; elsewhere, it comes out as crankiness, or at least concern, grousing about punk kids on “What I’m Here 4” and “Itz A Setup.” Sometimes it’s just a change of habits, rapping (multiple times) about the pleasures of taking a night off drinking; other times, it’s an earned weariness toward the bullshit side of the business, spoken from the other side of a record deal.

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Which isn’t to say that it’s all moralizing; on a pure line-to-line basis, it’s full of sharp turns of phrase. Guru’s animated by the change of perspective, but he’s still Guru. On the title track, he reflects, almost overwhelmed with emotion, on a weapons possession charge, but still can’t stop reminding us, “The apparatus gets blessed / And suckers get put to rest.” On “What I’m Here 4,” he decrees, full of righteous boom-bap authority, “Bob your head to it / There’s the water, you’ve been led to it.” There are flights of lyrical grandeur unlike any in his career, like when he sets a scene on “My Advice”: “Way past the days of the deuce, me and you stays a crew / Only a few percent knew what me and you went through.” On “Above The Clouds,” he sounds downright GZA-esque, rapping, “Bear in mind, jewels be the tools of the trade / Sharp veins, heavenly praise and dues are paid.” While the broader themes here are pretty unglamorous—growing old, dealing with debt, rueing mistakes past—Guru never loses the implacable cool of his delivery, the certainty of his skill on the mic.

Some of the album’s most affecting lines can scan as clunkers out of context. “The best way, it ain’t always the fast way,” he says on “Royalty”; on “What I’m Here 4,” he declares, “While some choose greed, I choose to plant seeds.” But over Premier’s luxurious production, and within the greater framework of Guru’s legal problems and career, it turns into a plainspoken call for mentorship, philanthropy, and self-reflection. This was a quiet, unfussy revolution. Rappers have always struggled with getting older. Most just keep firing off the clichés they got rich on; others downshift to acting (Ice Cube), the festival circuit (Big Boi), or whatever you’d call what Snoop does these days (celebrity?). JAY-Z never really figured out how to rap truthfully in middle age until last year’s 4:44. Moment Of Truth nails it while still providing everything we’d want from a Gang Starr record. It is the sound of hip-hop aging gracefully.

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You can debate exactly which moment of truth the album title is referencing—death, criminal sentencing, an argument about money, the first time you feel too old to be at a show—but I think the moment of truth is an artistic one. It’s the point when perhaps the zeitgeist has moved past you, perhaps you’ve lost a step, perhaps you’re in need of a comeback, and you rise to the moment not with nostalgia or a cash grab but with shocking, iconoclastic evolution. Guru, reeling from legal trouble and feeling like the world is forgetting the “real hip-hop” he helped define, determines simply to be better, as a man and as a rapper. In the album’s final, gauzy moments, as Primo calls out friends who have passed and Guru eulogizes others, the rapper concludes, “I pray each one will ascend to new heights and new enlightenment / And this is why I’m writin’ it.” The act of writing—of rapping—is itself a medium for transcendence, a way of marking the passage of time and the presence of life. It overflows on Moment Of Truth.